


Telling of the First Time

by anemptymargin



Category: Star Trek: The Next Generation
Genre: First Time, M/M, Underage - Freeform, flash back
Language: English
Status: Completed
Published: 2010-11-16
Updated: 2010-11-16
Packaged: 2017-10-13 05:44:43
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,958
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/133627
Author URL: https://archiveofourown.org/users/anemptymargin/pseuds/anemptymargin
Summary: <blockquote class="userstuff">
              <p>Wesley comes clean with Deanna about his past with Will, and then shows her exactly how it happened the first time.</p>
            </blockquote>





	Telling of the First Time

**Author's Note:**

> In continuity with Tomorrow, but not a sequel per se. Many thanks to (LJ) sexylaccolith for a basic beta read!

He had been aboard the Titan almost four weeks already, trying to make a name for himself outside of the boy genius he’d been an age before - even taking steps to further distance himself from his travels and just be a typical Starfleet officer. For the most part the transition had been seamless and he was content to let himself get lost in his role in engineering, Lieutenant Crusher. Of course he’d had reservations when the assignment came down, nobody had needed to tell him Captain Riker had requested him specifically and probably had to call in at least one favor given the high profile assignments he was up for. It had made sense to all involved for him to serve with familiar officers, and Wesley tried to take comfort in telling himself it was his skills that landed him where he was and not their history.

It was his destiny, he had been told as much and seen very vividly several points in his history to be that would get him there. The visions were left over from his travels, something he knew would never fully leave him - just flashes of moments without any sort of context or clarity - that told him when something would alter or fulfill his path. Usually they made no sense at the time and he had trained himself to not let them completely derail his life. It was a vision that interrupted his attempts to simply blend in and left him standing outside the Captain’s quarters at 07:00 hours after a fitful sleep.

“Wesley.” Deanna smiled as he entered, ushering him in towards a lovely breakfast she had already laid out.

“I’m sorry. I don’t mean to interrupt.” He replied, knowing full and well that he wasn’t - the vision was clear, they were meant to have the conversation over coffee and fruit… quite civil despite the typically difficult subject matter.

“You aren’t.” She pulled out a chair, entering his beverage selection into the replicator; “Coffee?”

“Sure.” He smiled, keeping up the pretense a little longer just to see what was to play out next.

“I remember.” She chuckled softly, shaking her head. “This may sound strange, but shortly after you joined the crew I had this same exact breakfast with you in a dream.” She paused, joining him at the small table. “Last night he told me you would come see me in the morning and I knew that it was true.”

Wesley nodded, “The Traveler, you saw him?”

She shook her head, “Will told me you were coming.” It was an interesting turn of events that Will should be guiding the conversation and not yet be present - though it would only be fair given the topic of discussion. “I suppose we have quite a bit to talk about.” Deanna licked her lips, starting things on the path before Wes could even think of where to begin.

He nodded again, letting himself simply consider both the situation and his friend. She didn’t know much about the past, but undoubtedly knew enough to make a wife suspicious or even upset… she appeared to be neither. “You don’t hate me?” He found himself smiling even as he asked.

“No.” She shook her head, picking up her mug in both hands. After a long pause she continued, “I was very angry for several years when he wouldn’t tell me what was happening. I knew it was bothering him and wanted to help, but he was afraid it would hurt all of us to tell me.”

“Would it have?”

She thought about it, lowering the mug and sectioning a bright red fruit he didn’t recognize before answering; “It would have changed things. I don’t know if it would have been for the better.”

“It’s supposed to be this way.” Wesley interjected before she could think further on it, “Things are happening the way they are supposed to.”

Deanna nodded slowly, stroking her fingertips over the flesh of the soft fruit she had been pulling apart. “He has never told me explicitly what happened, but I have bits and pieces that fit together in some fashion.”

“I see.” Wesley nodded; “Not literally, but I knew you put some of it together. Could you tell me more?”

“Of course.” Her smile faltered only a moment, thankfully she was quite at ease. “He loves you, even now… very deeply and in a way that I don’t know he has ever understood fully.” She paused again, clearly a bit hurt by the thought - with good reason. “It started when you were quite young. I know, he has associated you with a great amount of guilt and also passion.” She stopped, eating a small piece before continuing, “Something happened before you left, the tension between you changed to something it should not have.”

Wesley interrupted before she could continue. “We were lovers.” She didn’t respond, but Wes could feel a touch of both pain and understanding. “I was not quite sixteen when it started and it was never anything solid.” He barreled on, continuing to lay out the timeline as best he could. “It was over a few months before… before I left. It really all came down to me asking for something I wasn’t destined to have.”

She didn’t respond for several long minutes, and her emotions were once more hidden from him. Finally, she said; “You wanted him to be exclusive.”

He laughed unexpectedly, “Something like that.” He realized he was grinning again.

Slowly, her smile returned and she began to pick at her breakfast once more. A much more comfortable silence settled between them and he watched her eat with utmost admiration. She was taking the new knowledge quite well, probably only filling the gaps in what she already knew. She asked, “Would you be frank with me if I asked how it started?”

Wesley smiled wider, nodding as he stood up and moved close beside her. “I can show you.”

“Show me.” She whispered, not quite a question but not a demand.

Wes licked his lips and rested his hand gently on top of hers, “I’ve been waiting to do this… you’re my first.” It was true. He’d been told before he left he would be able to share his memories, but must only do so with someone he trusted intimately with such a deep bond. Clasping her hand tight, he knelt on the floor beside her and whispered, “Just listen to my voice and let down your walls.” It felt right, at least. “I’ll show you everything and let you see my side of the story.” She nodded assent and waited quietly. “Deanna. Don’t be afraid, I’m in your thoughts now.” He spoke, without speaking and couldn’t help but wonder if it was just as simple when she spoke telepathically. It wasn’t true telepathy really, only a one way mirror… like watching a holodisc of his narration of his own memory. He couldn’t control or alter the message, only show and tell. “I know you blame Will for all of this, he blames himself too but that’s something we’ll have to address another day. I started it, Deanna. I was young and impulsive… and determined to get what I wanted.”

***

“Commander…” I moaned against my fist, biting down into my knuckles to stifle the sound. My muscles clenched and I pushed back against the wave of pleasure, stroking hard and strong until I finally came - resisting the urge to bite down even harder and just let loose. I was sixteen, sexually frustrated and utterly enamored with the Commander. It’s funny, Deanna… but for almost the first year I couldn’t see past Starfleet ranks… I wonder if that’s why it was so thrilling at first to seduce and ultimately have someone in authority. Regardless, I had my suspicions that his thoughts were less than pure - he liked to touch too much… to look too long, the sort of poetic sounding thing that may have well been all in my head at the time. I asked him once, not long before we broke things off for good, when he noticed the potential and he claimed it wasn’t until I was naked in his lap - but with that laugh right afterward that gave him away.

I cleaned up and put on my uniform, stretching the taut fabric until it looked just right. My day was uneventful, seemingly one thing after another leading to the event I looked forward to most of the day - passing Commander Riker in the corridor and perhaps taking the turbolift if he was off shift. Thankfully I’d been in luck.

“Deck 8.” Will spoke as he entered the lift, smiling when I managed to slip in behind him.

“Deck 10.” I added quietly. The lift paused a moment, then began its usual trip in near silence. Finally mustering up the courage, I asked quietly; “If you’re not doing anything later on, sir, I was wondering if you would be free to look at a program I’ve been working on for the holodeck.”

At first he didn’t respond, and I wondered if I had spoken at all, but then as the lift stopped he turned to me a smiled, the tip of his tongue running along the bottom of his lip before he responded. “Sure, a bit of relaxation?”

“Yes! Of course.” I jumped at the opportunity being accepted so easily. It sounds pretty terrible now, but when I didn’t know better it seemed like the ultimate in smooth suggestion. “Fifth Century Greece.” I smiled, already feeling warm behind the ears. “You don’t have to wear a costume or anything special.”

He seemed to be considering the offer again, giving me the sinking feeling he was trying to find some way to bow out without coming off badly. Then once more, his lips quirked into a curious smile. “Alright. Give me an hour.”

I wanted to explode then, I think. Everything was falling into place far too easily. When he stepped out of the lift I practically danced to the holodeck. For that whole hour I obsessed over every minute detail of the small bathhouse scene; the temperature, sculptures, plant life, even the lighting had to be precise. When he came several minutes early, I was still tying off my plain white towel.

“Wesley.” He spoke calmly, approaching where I stood as he examined the environment. I imagined he was staring at me, hoping in many ways that he was.

“You like it?” I grinned, tossing him a towel.

He nodded, stopping not even a foot away. “You really wrote this, huh?”

I stepped towards the warm inset pool, down the stone steps until water lapped at my ankles. “It's sort of been a pet project.”

He grinned wider and watched me sit at the edge, letting the towel bunch around my waist. Almost too casually, he stripped off his uniform. I looked, I mean… I was sixteen and pretty much getting painfully close to exactly what I wanted. He was close to what I had imagined, and definitely at least a little aroused by the situation. As if consciously confirming my desire and his attraction, he walked closer and dropped his towel between us. “When in Corinth?” He chuckled under his breath, lifting an eyebrow.

Hah, thinking about it now I just stared at him as he sat down on the edge of the pool - close enough to touch. In retrospect he made it pretty damn clear he knew exactly where I was taking things. “I was going for Athens.” I responded dumbly, not really sure where I was taking things anymore.”

He laughed out loud, somewhat unexpectedly, and blushed red across his jaw line. He tugged the towel over his lap as though he’d just realized the moment that had passed, “It’s really nice, Wesley.” He looked down into the water, swirling it around his feet.

“Thank you.” I responded, quietly adding, “Sir.”

He chuckled again and shook his head. For a long moment he was quiet - enjoying the soft sounds of the empty bathhouse. Perhaps frustrated, perhaps bold, he looked back from his lap to me. “So,” he spoke almost with a sense of apprehension, “How long should I wait before pointing out the obvious?”

“Sir?” I pretended to be innocent, getting the sinking feeling in the pit of my belly that things weren’t going quite as well as I’d initially assumed they were.

He licked his lips and looked away, “You’re about as subtle as a Klingon.” He let out another soft chuckle, shaking his head, “It may have been somewhat more subtle to pin me down and break my legs.”

I froze, I hadn’t expected he would piece things together until well into the final stages of my plan… and honestly assumed that if he did he would have at least kept quiet about it. Of course as far as plans go, mine hadn’t been a very good one. “What do you mean?”

At first he didn’t answer, merely slid out from under the towel that had been covering his nakedness and into the warm pool. After thinking it over for a bit, he responded, “I think you ought to know that if we’re going to play this game it isn’t going to go where you think it will.” In the long run, he was right - but that’s a bit of a long story. He dipped down under the water, and then found a small, comfortable, spot to break the surface and relax on the opposite side of the recess.

Figuring my cause was getting pretty desperate, I took to desperate measures and unknotted my towel. My whole body blushed as I exposed myself to him, “Please don’t go.”

Will watched me very intensely, even before that moment, and I think I knew even then that he wasn’t about to leave. I know now that even his protests were for the sake of his own conscience more than anything else. When he made no move to do so, I stepped into the shallow water, wading over to where he sat chest deep.

He leaned back, too casually really, and looked me dead in the eyes. “You shouldn’t do this, Wes. I understand that you think you want this - but you don’t.”

He was wrong, but I understand that at the time he didn’t know it. Sometimes I think he still doesn’t realize that I was always well aware of my actions. Later in our relationship, I used sex against him. All it has ever taken to get what I want is to push the right sequence of buttons… it was too easy. I stood as close to him as I could, his knees brushing against my thighs. “And what do I want, Sir?”

“Someone your own age. Someone who isn’t desirable just because they’re an authority figure.” He paused, probably realizing those things were irrelevant when stripped naked and aroused. “One of your peers.”

I had to laugh; “My peers?” I responded incredulously, “You mean the kids in my class? Come on, you’ve got to know by now that I don’t belong there. I belong on the bridge - even you have said I deserve rank.” I forced myself to stop and focus on the moment at hand before I blew it completely with my own stupid ego. Boldly, I climbed up into his lap, straddling him with one knee pressed tight against each of his thighs. “I belong here. With you.” I pushed as close as I could, chest to chest as I fit myself against his body like we’d always been meant to be that close. “I want you.” The words come out far more whiny and childish than I had intended, but apparently they worked.

Almost unexpectedly, he grabbed me by the chin and pulled my mouth close for the hardest kiss I’d ever had - not that there was much to compare it to. It was rough, aggressive… much more so than I had imagined it would be. Both of his large hands stroked down my shoulders and chest - then held me tight at the waist. “Is this what you want?”

I must have been grinning like an idiot again, no matter how poorly planned or executed everything was pretty well looking up. Sure I could ask for just about anything at that point, I reached down into the water and slipped a hand directly behind me - eagerly grasping his mostly hard manhood and guiding it against my ass. He chuckled nervously, but the shift of his cock pressing even harder against me gave it away. “This is what I want.”

I would apologize for my graphic verbiage, Deanna, though I feel that you are much more intrigued than offended. I won’t pretend to be shocked.

His reaction… well, I believe that isn’t shocking either. He smiled, his body even warmer than the bath, and kissed me once more. Not hard the second time, but clearly deliberate. Slowly, he stroked back up to my shoulders, and then touched my face with his palms. I figured he must still be reluctant and broke off the kiss to whisper; “Please. Please, Will…” It was the first time I had called him by name, and in my head it sort of stumbled off my tongue… it didn’t really ever feel right until after I had left for the academy.

He shook his head, still wearing a lopsided smile; “Are you sure you want me to be your first?”

I nodded even as I couldn’t help but ask; “What makes you think you’re first?”

“You asked me to meet you in ancient Greece to play into a subconscious pederastic fantasy encouraged at that point in history.” He ran his tongue over the inside of his lower lip, punctuating the thought. “What you lack in subtlety you make up for in having the courage to follow through with it.”

“Is it working?” I couldn’t stop myself; something just made me want to keep talking despite my body’s desire to shut up.

He paused, and then kissed me again and again. It was working. “I want to show you something.” He murmured between kisses. When he spoke again it was to address the computer, calling up a private locked program. Gone were the warm water and steam - Grecian architecture replaced by the interior of a small, drab room. The towels lay forgotten by the door as Will braced himself to the shift of my weight in his lap. “Alaska, 2348.”

I held tight to him, pulling up my legs and wrapping them around his waist - encircling his chest with my arms. My eyes searched every bit of the room - but it could have been any cheap hotel on Earth… or several other planets for that matter. Bed, table, two chairs, a small view screen. Only a single window showed the outside world, a parking lot covered in great mountains of snow with more falling fast.

He continued, “She was a few years older than I was, already doing admirably in her research as a medical technology specialist.” I watched as the holographic pair came in from the cold, laughing and shaking off the snow as they disrobed - leaving a trail of slush and clothing to the bed. “Computer, end playback. Remove characters.” He ordered, just as things were starting to get interesting. “She was my first.” He let out a dray chuckle, hugging me tighter to him. “It was absolutely awful; we were both embarrassed and haven’t talked to each other since.”

I was confused; “Why are you showing me this?”

“This will change everything, if we go through with what you’re suggesting. We could stop right now, put on our uniforms and go back to not doing something we will probably regret.”

I grinned and flattened my palms on his back - enjoying the sensation of his bare flesh pressed completely against my body. “Or we could not.”

“True.” He responded honestly, letting out a soft sigh when I leaned in even further, pushing him backwards as I rested my head on his shoulder. “You do realize it would have to be kept in the strictest confidence.”

I laughed, a bit of my remaining nervousness assuaged. “My mother would kill you.”

“Only after I was court-martialed. This directly violates at least one Starfleet regulation.”

I grinned, my lips gently kissing his bare chest - seeking out the skin. “Since when have you thought regulations are more than a suggestion?”

He groaned softly when my mouth found a nipple, suckling it between my lips. “Mmm, I won’t say that you make a pleasing argument for them.” A strong hand stroked over my hair and he whispered; “Only if you’re sure.”

I opened my lips, letting out the hard bud before I had intended to. Still feeling empowered by the knowledge of his mutual attraction I shifted my weight forward again, somehow managing to push him to the floor. He grunted, but kept smiling when I let my body lay completely atop him. “More than anything.”

He nodded slowly, watching my eyes - perhaps for the possibility of deception or regret. “We’ll do this my way. Get up on the bed.”

It was everything I could do not to say; “Yes Sir” as I scrambled off of him and onto the bed. I can’t believe I’m letting you see this, but I suppose you deserve a little bit of the horrible to go with the good. I just got right up there and put my ass up in the air like it was the perfect thing to do.

He laughed at me. I mean, if I hadn’t clearly been out of my element I would have been offended, but I guess he knew far better than I did. “It doesn’t exactly work like that, Wesley.” He pushed himself up off the floor and remained standing beside the large holographic hotel bed. I still wonder what was going through his mind as he watched me with those eyes that looked like he could eat me alive. After that moment I became much more aware of when he was looking at me. “Roll on your back.”

I did as he told, feeling only the slightest hint of shame when I exposed myself to him - my first instinct to grasp my manhood by the base and stroke it out towards him with my opposite hand. He smiled and licked his lips, the response only urging me further.

“Slowly, slow…” He spoke more softly than I’d ever heard him, sinking down onto the mattress to lay the opposite direction - taking full control he straddled me on all fours, affording me a view that was pretty amazing at the time.

I’ll admit, as though it isn’t painfully obvious, he was my first… first everything, but when you’ve got something just right there in your face like that I think instinct sort of takes over. His mouth felt better than anything I’d managed on my own… or once with a program I don’t particularly care to remember. It’s pretty embarrassing, but I’m sure you can imagine I didn’t exactly last long. I was still barely exploring his cock - kissing and licking at the hard shaft before experimentally taking what little I dared between my lips. He tasted… well, I guess you probably know but it was amazing in my mind. I didn’t even take it all in before my knees started to buck le and he pushed down hard on my hips - pinning me down. I’m not sure what worked for me more… that he wanted me to get off or that I was actually doing it.

He pulled away from me unexpectedly as I rode the hard waves of orgasm; I must have whined pretty loudly because he turned to look me in the face again. He was blushing dark, his breathing hard and ragged. “Is it still what you want?” he panted.

I would have done anything for him at that moment. If he had asked in that tone of voice, I could have lied, probably even killed. I just wanted him to feel even close to how I was at that moment. “Please?” I begged, not even knowing really what I was asking for.

He nodded and swallowed hard, holding out an open palm. “Computer, replicate compound 697-P. Two ounces.”

I was lost, but thankful he was taking charge. The small dish appeared in his hand and he guided my knees up and open. By the time I had fully put it together he was gently rubbing the slippery concoction over my opening. “Will it hurt?” I asked naively.

He nodded again, dragging his first two fingers through the goo and then across the opening once more - teasing very lightly. “Not as much as a Grecian boy.” He smiled briefly, and then added; “There is a slight numbing agent in the mix - it’s based on something a good friend of mine found on shore leave at Risa.”

I won’t say that I wasn’t the slightest bit afraid, but I will tell you he was gentler than I ever thought he could be. He took it very slow, easing me open with his fingers until I was trembling and moaning - barely able to stand the anticipation. “Please….” I begged him, meaning it this time. I wanted more, I wanted… I wanted to please him.

“Look at me, Wesley. I want to see your eyes.” He requested, slowly withdrawing the three fingers he had been working me over with.

I won’t say that was easy to look him in the face, in a way it completely solidified what was happening. We were well beyond the point of turning back, and what was left of what he considered my innocence was lost. I think part of me wanted him to be conflicted, that it would have been better if he had faltered and at least pretended it wasn’t what he wanted. I can’t explain it, but that was the only time I didn’t know for sure if it was all real. I looked into his warm eyes, seeing lust but beyond that something I couldn’t decode at that time - it was fear. He was afraid of what it all meant, probably of what would come of it… if anything at all.

“You’re beautiful.” He whispered as he pulled me in tight against his hips, rubbing the slick tip of his cock against my stretched out hole.

My whole body was flushed pink and damp with a light sweat that I can only assume was much more beautiful right before you got ready to engage in something incredibly intense with someone. I forced a smile and looked away, to that single window now buried in the snow outside. He pushed himself in slowly, then took me by the hips with both hands - hilting inside me hard. Self conscious, I pushed my own palm over my mouth - holding back the loud moans as he began to withdraw and thrust in decidedly slow rhythm. I closed my eyes, turning my palm to the side and biting down between my thumb and forefinger as I let myself get lost in the sensations.

“Wes…” He panted softly, picking up speed - each thrust harder and faster than the previous. “Look at me, Wes. Are you okay?” I moaned around my hand, rocking my hips up against him only to have my knees knocked apart once more. Slowly, I opened my eyes to watch his face twist as he let out a low, growling sound. Without even thinking about it, he pulled out and came on the bed - his shoulders rolling as he pushed up and stretched out his back. For a moment his whole being seemed impossibly big, only to be dashed again when he collapsed beside me.

I don’t really remember how I felt about it once it was over, I guess that’s the sort of thing you’re actually supposed to remember… but all I could think about was that it had finally happened. I curled up against him and showered kisses on his shoulder until he held me in his strong arms. Then, without a word we parted. He just pulled on his uniform and left.

***

“You were hurting.” Deanna spoke softly as Wesley’s voice stopped - the images ending as suddenly as they had started. “Figuratively, I mean… he changed.”

“Because of what I did.” Wesley responded. He returned to the chair he had previously occupied, swallowing hard before adjusting his obvious arousal and forcing himself to sit down. “It was pretty crazy, I guess… but that’s the way it was then. I don’t think he even talked to me for a week after that.”

“He had to think about what he had done.” Deanna answered the question before he could even answer it. “His identity had shifted to include you.”

“But who was I, really? I was nothing to him.” Wes sounded almost hurt, his voice dropping to a soft murmur as he picked up a piece of fruit to roll in his hands. “I was just some horny kid with an authority complex.”

Deanna sighed, “We both know that isn’t true, Wesley. If you expect to work things out you’ll have to get over the past.”

He nodded slowly, “I know, I just feel kind of stupid about the whole thing. I don’t know why I’m even here or why I’m telling you any of this.”

“I want you to. I want to know.”

“But why? What could it possibly solve?” She didn’t answer, didn’t have to really. Before Wesley could push it any further his com chirped, reminding him he had places he should consider being.

“Come tonight, Wesley. I want to know more.”

***End***

**Author's Note:**

> This is a work of fictional parody in no way intended to infringe upon the rights of any individual or corporate entity. Any and all characters or celebrity personae belong to their rightful owners. Absolutely no money has or will be gained from this work. Please do not publicly link, repost or redistribute without letting me know first.


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